Diethyl[2-(2-methyl-4-nitrophenoxy)ethyl]amine → N-[2-(4-Amino-2-methylphenoxy)ethyl]-N,N-diethylamine

HRID 898547Notes

Reaction equation

HRID 898547 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[CH3:16])[CH3:2]>C(OCC)(=O)C.[Ni]>[CH2:17]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[CH3:16])[CH3:18]

Participants

4

Reactant 1

HCID 68816853Diethyl[2-(2-methyl-4-nitrophenoxy)ethyl]amine

Product 1

HCID 26189998N-[2-(4-Amino-2-methylphenoxy)ethyl]-N,N-diethylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.10 g (12.3 mmol) diethyl-[2-(2-methyl-4-nitro-phenoxy)-ethyl]-amine were dissolved in 250 mL ethyl acetate, 0.55 g Raney nickel was added and the mixture was hydrogenated for 36 hours at 50 psi and ambient temperature. The catalyst was filtered off and the filtrate evaporated down i. vac.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated down i

Sources & evidence

ORD record
ord-07769d93a6aa47128b8a0fcf961dd42b
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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